Vat dyestuffs of the anthraquinone series



Patented Dec. 12, 1933 I v .f..j; 1 938,aes -VAT-DYESTUFFS OF THE ANTHRAQUINONE' SERIES Otto Bayer, Frankfort-on-the-Mai'n, Germany,

assignor to General Aniline Works; Incl, New 7 York, N. Y., a corporation of Delaware No Drawing. A ppl icai doniltl arch 7, 19. 3, Serial N. 597,429, andinfiermany Marelrlg, 1931 ..3.-Claims. (o1. 250 s The-present invention relates to vat 'dyestufls of-the anthraouino'ne-series' In accordance withthe invention new vat dyestufls of thearithraquinone series are prepared I by causing one molecular proportion of a metaor para-diphenylb'enzene dicarboxylic acid or a substitution product thereof, or, more advantageously, of a functional derivative of these compounds (the halides, for example) to react on '10 two molecular proportions of alpha-aminoanthraquinone or a substitution product thereof.

Suitable substituted alpha-aminoanthraquinones are, for example, those; as are substituted in the The diphenylbenzene" dicarboxylic acids in "question can be prepared, for example, by reacting upon metaor para-diphenylbenzene with acetylchloride according to the Friedel-Crafts reaction and oxidizing the reaction products ,9,wlth chromic acid in glacial acetic acid. The "halides can be prepared from the dicarboxylic acid thus obtained according to one of the meth- Ods generally applied in the manufacture of carboxylic acid halides from carboxylic acids.

' The new. dyestufls probably correspond to the general formula;-

wherein the various nuclei maybe substituted by monovalent substituents and wherein the benzene nucleus marked II is attached to the benzene nucleus marked I in the 3- or 4-position. They form yellow to bluish-red powders dinicultly soluble in the usualorganic solvents, soluble in concentrated sulfuric acid with a yellow ...shade of excellentfastness properties andvery coloration, dyeing c'otton from analkaline hydrosulflte vat yellow tcblu'ish red shades of good fastness properties. "The new dyestuifs are generally distinguished from the known dyestufis of similar structure-by a better 'capacity of being absorbed by the fibre, by improved dyeing power and by the fact that they are fast to kier boiling.

The following examples illustrate the invention, without, however, limiting it thereto:-

.1 Example 1 30 kgs. of para-para-diphenylbenzene-dicarboxylic acid are-heated to boiling in about 500 kgs. of ortho-clichlorobenzene with 35 kgs. of thionylchloride, until complete solution has been rought about. Then, advantageously after distilling off the excess of thionylchloride, 46 kgs. of alpha-aminoanthraquinone are added and the whole is heated to boiling for about 2 hours, until the evolutionof hydrochloric acid has ceased.

The dyestufl, which separates in yellow crystals,

is filtered off while hot and washed with alcohol.

It dyes a clear and powerful greenish-yellow satisfactory aflinity for the fibre from a hot or cold bordeaux-red colored vat.

Example 2 When in Example 1 the para-para-diphenylbenzene dicarboxylic acid chloride is replaced by an equal quantity of 1.3-dipheny1benzene-dicarboxylic acid chloride a very similar dyestuif is produced, which dyes a somewhat more greenish yellow shade than that of Example 1. V

When instead of the. alpha-aminoanthraquin- 0:2 o 2 one derivatives thereof are employed, such as for example, 6-chloro-l-aminoanthraquinone, l-amino-4- or -5-benzoylaminoanthraquinone or 1- amino-4-methoxy-anthraquinone' valuable dye- 11 stuffs are likewise obtained.

I claim: 1. The compounds of the probable formula:--

the usual organic solvents, soluble in concentrated sulfuric acid with a yellow coloration, dyeing cotton from an alkaline hydrosulfite vat clear and strong yellow to-bluish-red shades of good fastness properties. a

- 2; The compoundsot'the formula:

wherein the benzene nucleus marked II is attached to the benzene nucleus marked I in the 3- or 4-position, said compounds forming yellow crystals, dyeing cotton strong yellow shades of excellent fastness properties.

3..A compound of the formula:

said compound forming yellow crystals dyeing cotton from a bordeaux red colored vat greenishyellow shades of an excellent fastness and a satisfactory afiinity to the fiber. v

O'I'IO BAYER. I 

